1-methyl-1,3-diazinane-2,4,6-trione

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-Methylbarbituric acid (10 g) was suspended in phosphorus oxychloride (70 ml). Water (2 ml) was added and the mixture was heated at reflux for 40 minutes. The reaction was allowed to cool and was then concentrated under reduced pressure. The residue was poured onto a mixture of ice and water (200 ml). When the ice had melted, the precipitated solid was collected, washed with water and dried in vacuo at 50° C. to give the sub-title compound (6.86 g) as a yellow solid. the mixture was heated at reflux for 40 minutes to cool was then concentrated under reduced pressure The residue was poured onto a mixture of ice and water (200 ml) the precipitated solid was collected washed with water dried in vacuo at 50° C.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-Methylbarbituric acid (10 g) was suspended in phosphorus oxychloride (70 ml). Water (2 ml) was added and the mixture was heated at reflux for 40 minutes. The reaction was allowed to cool and was then concentrated under reduced pressure. The residue was poured onto a mixture of ice and water (200 ml). When the ice had melted, the precipitated solid was collected, washed with water and dried in vacuo at 50° C. to give the sub-title compound (6.86 g) as a yellow solid. the mixture was heated at reflux for 40 minutes to cool was then concentrated under reduced pressure The residue was poured onto a mixture of ice and water (200 ml) the precipitated solid was collected washed with water dried in vacuo at 50° C.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-Methylbarbituric acid (10 g) was suspended in phosphorus oxychloride (70 ml). Water (2 ml) was added and the mixture was heated at reflux for 40 minutes. The reaction was allowed to cool and was then concentrated under reduced pressure. The residue was poured onto a mixture of ice and water (200 ml). When the ice had melted, the precipitated solid was collected, washed with water and dried in vacuo at 50° C. to give the sub-title compound (6.86 g) as a yellow solid. the mixture was heated at reflux for 40 minutes to cool was then concentrated under reduced pressure The residue was poured onto a mixture of ice and water (200 ml) the precipitated solid was collected washed with water dried in vacuo at 50° C.

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Water (2.7 mL) is added dropwise to a suspension of 1-methylpyrimidine-2,4,6(1H,3H,5H)-trione (14.2 g, 100 mol) in POCl3 (95 mL) at 0° C. The reaction mixture is then heated at 80° C. for 5 hours. The resulting brownish solution is cooled, and POCl3 is evaporated under reduced pressure. The residue is treated with MeOH, and the obtained solid is recrystallized from ethanol to give 11.5 g product (Yield: 71.6%). m.p.=279-282° C. (dec) [Lit.2: 280-282° C.]. 1H NMR (400 MHz, DMSO-d6) δ 3.10 (S, 3H), 5.90 (S, 1H), 12.4 (br, 1H). The resulting brownish solution is cooled POCl3 is evaporated under reduced pressure The residue is treated with MeOH the obtained solid is recrystallized from ethanol

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of malonic acid (80 g, 0.79 mol) and methylurea (50 g, 0.68 mol) in 180 ml of acetic acid at 70° C., acetic anhydride (130 ml, 1.37 mol) is added slowly. After the completion of the addition, the reaction mixture is stirred at 90° C. for 3 hours, and then cooled to room temperature. The solvent is removed under reduced pressure, and the residue is treated with 350 mL of ethanol to precipitate out yellowish solid. The solid is recrystallized from ethanol to give 63.1 g product as crystalline solids (Yield: 65.8%). m.p.=131.2-133.1° C. [Lit.1: m.p.=130-131.5° C.]. After the completion of the addition cooled to room temperature The solvent is removed under reduced pressure the residue is treated with 350 mL of ethanol to precipitate out yellowish solid The solid is recrystallized from ethanol

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of malonic acid (80 g, 0.79 mol) and methylurea (50 g, 0.68 mol) in 180 ml of acetic acid at 70° C., acetic anhydride (130 ml, 1.37 mol) is added slowly. After the completion of the addition, the reaction mixture is stirred at 90° C. for 3 hours, and then cooled to room temperature. The solvent is removed under reduced pressure, and the residue is treated with 350 mL of ethanol to precipitate out yellowish solid. The solid is recrystallized from ethanol to give 63.1 g product as crystalline solids (Yield: 65.8%). m.p.=131.2-133.1° C. [Lit.1: m.p.=130-131.5° C.]. After the completion of the addition cooled to room temperature The solvent is removed under reduced pressure the residue is treated with 350 mL of ethanol to precipitate out yellowish solid The solid is recrystallized from ethanol

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Water (2.7 mL) is added dropwise to a suspension of 1-methylpyrimidine-2,4,6(1H,3H,5H)-trione (14.2 g, 100 mol) in POCl3 (95 mL) at 0° C. The reaction mixture is then heated at 80° C. for 5 hours. The resulting brownish solution is cooled, and POCl3 is evaporated under reduced pressure. The residue is treated with MeOH, and the obtained solid is recrystallized from ethanol to give 11.5 g product (Yield: 71.6%). m.p.=279-282° C. (dec) [Lit.2: 280-282° C.]. 1H NMR (400 MHz, DMSO-d6) δ3.10 (S, 3H), 5.90 (S, 1H), 12.4 (br, 1H). The resulting brownish solution is cooled POCl3 is evaporated under reduced pressure The residue is treated with MeOH the obtained solid is recrystallized from ethanol

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of malonic acid (80 g, 0.79 mol) and methylurea (50 g, 0.68 mol) in 180 ml of acetic acid at 70° C., acetic anhydride (130 ml, 1.37 mol) is added slowly. After the completion of the addition, the reaction mixture is stirred at 90° C. for 3 hours, and then cooled to room temperature. The solvent is removed under reduced pressure, and the residue is treated with 350 mL of ethanol to precipitate out yellowish solid. The solid is recrystallized from ethanol to give 63.1 g product as crystalline solids (Yield: 65.8%). m.p.=131.2-133.1° C. [Lit.1: m.p.=130-131.5° C.]. After the completion of the addition cooled to room temperature The solvent is removed under reduced pressure the residue is treated with 350 mL of ethanol to precipitate out yellowish solid The solid is recrystallized from ethanol

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Water (2.7 mL) is added dropwise to a suspension of 1-methylpyrimidine-2,4,6(1H,3H,5H)-trione (14.2 g, 100 mol) in POCl3 (95 mL) at 0° C. The reaction mixture is then heated at 80° C. for 5 hours. The resulting brownish solution is cooled, and POCl3 is evaporated under reduced pressure. The residue is treated with MeOH, and the obtained solid is recrystallized from ethanol to give 11.5 g product (Yield: 71.6%). m.p.=279-282° C. (dec) [Lit.2: 280-282° C.]. 1H NMR (400 MHz, DMSO-d6) δ3.10 (S, 3H), 5.90 (S, 1H), 12.4 (br, 1H). The resulting brownish solution is cooled POCl3 is evaporated under reduced pressure The residue is treated with MeOH the obtained solid is recrystallized from ethanol

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of malonic acid (80 g, 0.79 mol) and methylurea (50 g, 0.68 mol) in 180 ml of acetic acid at 70° C., acetic anhydride (130 ml, 1.37 mol) is added slowly. After the completion of the addition, the reaction mixture is stirred at 90° C. for 3 hours, and then cooled to room temperature. The solvent is removed under reduced pressure, and the residue is treated with 350 mL of ethanol to precipitate out yellowish solid. The solid is recrystallized from ethanol to give 63.1 g product as crystalline solids (Yield: 65.8%). m.p.=131.2-133.1° C. [Lit.1: m.p.=130-131.5° C.]. After the completion of the addition cooled to room temperature The solvent is removed under reduced pressure the residue is treated with 350 mL of ethanol to precipitate out yellowish solid The solid is recrystallized from ethanol

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Water (2.7 mL) is added dropwise to a suspension of 1-methylpyrimidine-2,4,6(1H,3H,5H)-trione (14.2 g, 100 mol) in POCl3 (95 mL) at 0° C. The reaction mixture is then heated at 80° C. for 5 hours. The resulting brownish solution is cooled, and POCl3 is evaporated under reduced pressure. The residue is treated with MeOH, and the obtained solid is recrystallized from ethanol to give 11.5 g product (Yield: 71.6%). m.p.=279-282° C. (dec) [Lit.2: 280-282° C.]. 1H NMR (400 MHz, DMSO-d6) δ3.10 (S, 3H), 5.90 (S, 1H), 12.4 (br, 1H). The resulting brownish solution is cooled POCl3 is evaporated under reduced pressure The residue is treated with MeOH the obtained solid is recrystallized from ethanol

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of malonic acid (80 g, 0.79 mol) and methylurea (50 g, 0.68 mol) in 180 ml of acetic acid at 70° C., acetic anhydride (130 ml, 1.37 mol) is added slowly. After the completion of the addition, the reaction mixture is stirred at 90° C. for 3 hours, and then cooled to room temperature. The solvent is removed under reduced pressure, and the residue is treated with 350 mL of ethanol to precipitate out yellowish solid. The solid is recrystallized from ethanol to give 63.1 g product as crystalline solids (Yield: 65.8%). m.p.=131.2-133.1° C. [Lit.': m.p.=130-131.5° C.]. After the completion of the addition cooled to room temperature The solvent is removed under reduced pressure the residue is treated with 350 mL of ethanol to precipitate out yellowish solid The solid is recrystallized from ethanol